Next Article in Journal / Special Issue
A Survey on the Reactivity of Phenyliodonium Ylide of 2-Hydroxy-1,4-Naphthoquinone with Amino Compounds
Previous Article in Journal / Special Issue
Oxidative Dearomatization of Phenols and Anilines via λ3- and λ5-Iodane-Mediated Phenylation and Oxygenation
Molecules 2005, 10(1), 217-225; doi:10.3390/10010217
Article

Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones

 and *
Department of Chemistry, The University of Akron, USA
* Author to whom correspondence should be addressed.
Received: 5 July 2004 / Accepted: 14 July 2004 / Published: 31 January 2005
(This article belongs to the Special Issue Hypervalent Iodine)
Download PDF [209 KB, uploaded 18 June 2014]

Abstract

The conversion of α-benzocycloalkenones to homologous β-benzocyclo-alkenones containing six, seven and eight-membered rings is reported. This wasaccomplished via a Wittig olefination-oxidative rearrangement sequence using[hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis ofregioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation ofcarbon-13 at C-1 of the β-tetralone nucleus was also demonstrated. The Wittig-HTIBapproach is a useful alternative to analogous sequences in which Tl(NO3)3·3H2O or thePrevost combination (AgNO3/I2) are employed in the oxidation step.
Keywords: [Hydroxy(tosyloxy)iodo]benzene; benzocycloalkenones; ring expansion; oxidative rearrangement [Hydroxy(tosyloxy)iodo]benzene; benzocycloalkenones; ring expansion; oxidative rearrangement
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Justik, M.; Koser, G. Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones. Molecules 2005, 10, 217-225.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert